


Dean Winchester Loves Panties and Blue Eyes

by Supernatural_freak



Category: Supernatural
Genre: Bottom Dean, Bullying, Castiel is awesome, Highschool AU, Homophobia, Homophobic Language, I'm Bad At Tagging, M/M, Masterbation, Panty Kink, Smut, This is turning into a longer fic then I planned, Top Castiel, but dean handles it, cute fluff, dean loves panties, like really loves them, some porn
Language: English
Status: Completed
Published: 2014-03-06
Updated: 2015-12-26
Packaged: 2018-01-14 17:46:12
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 9
Words: 20,798
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1275370
Author URL: https://archiveofourown.org/users/Supernatural_freak/pseuds/Supernatural_freak
Summary: <blockquote class="userstuff">
              <p>Dean Winchester comes off as your normal, average every day jock. But what the kids at school don't know is that the famous Dean Winchester secretly has a stash of soft satiny panties hidden under his bed and the biggest crush on the guy who works at the retail store. This is a story about what happens when said crush catches one Dean Winchester looking at panties in the store he is currently working at.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> So this is just a little thing I threw together for my friend who basically gave me the prompt for this. None of the updates will be very long and they will be sporadic. This isn't like a full blown story, just a cute little thing. I also know I am not the best writer so please forgive my probably many mistakes (especially tenses). 
> 
> But other then that, enjoy!!! 
> 
> Comments and kudos greatly appreciated

Dean Winchester was probably the manliest man around, or so any of his friends would say, and if you went to school with him you would probably be under the same impression. Dean was the stereotypical jock, the one who was the star varsity baseball player, the one who got all the girls, the one who listened to classic rock and loved cars, and the one who was totally, 100% completely heterosexual, or so it seemed. 

But like every teenager, Dean Winchester had his secrets. They probably weren't your usually teenage secrets, the ones where you sneak alcohol at the parties or try to hide your porn magazines from your parents, or you slept with your best friends girlfriend. For Dean, his secret was in fact that he had a small stash of silky, soft panties hidden in a box under his bed, and whenever he was alone he would pull them on and enjoy the feel of the soft silk wrapping around his balls, and the feel of them tight in his ass crack. He would strut around thinking about how amazing it would be for someone to push him down and mouth the hard line of his cock through the panties. Dean also had to admit his ass look pretty awesome in those silky pieces of cloth.

There was one other secret Dean Winchester had and that was his giant crush on the blue eyed teen who worked at the local retail store. On days when he didn't have to take care of Sam or if he wasn't at school late for practice or working; Dean would sneak over to the store and hide behind the racks of clothes just watching the boy. His name tag read Castiel from what Dean could see from the distance he kept, but Dean had started to call him Cas. This crush had probably been going on for about a month now and Dean still hadn't gotten the courage to go talk to Cas. He was sure that this was just a phase and it would all pass and he could forget that any of this ever happened and assure everyone that Dean Winchester was straight.  
But you see things never really go as planned, especially not for a Winchester. 

Finally It happened one Friday evening. Sam had come home and Dean had notice that yet again his pants were showing way too much ankle to probably even be called pants. Dean was pretty sure that if his brother didn't stop growing soon that they wouldn't have enough money left to buy him clothes. With a dramatic sigh, and a text to his friends to cancel their plans for the night, Dean dragged Sam to the store to buy him some new clothes. To Sam, Dean was being his normally bitchy self, upset that he had to cancel his night out, but in all honestly, Dean’s stomach was full of butterflies at the thought of getting to see Cas again. 

When the two walk into the store ten minutes later, Deans eyes automatically searched for that familiar tuft of thick black, messy hair, and piercing blue eyes but much to his disappointment, Cas was no where to be seen. Dean shoulders slumped forward and he pushed Sam off to go find his clothes while Dean wondered around the store sulking. 

Eventually, the teen found himself wondering off to the women’s apparel section of the store. Making sure no one else was around, Dean wondered over to the panties aisle and admired the assortment of different panties. He noticed a soft looking pair with lace and Dean couldn't help himself when he reached forward and pulled it out of the pile. His fingers let the material slide through them and Dean felt himself harden a little at the thought of how this would feel, how nice the lace would look around his ass and how soft the silk would feel on his balls. Dean was so lost in his thoughts he didn't hear the sound of foot steps approaching until the person cleared his throat. Then a rough, deep voice, that caused the hairs on the back of Deans neck to stand up, said, “Can I help you sir? Are you looking for a gift for someone?” 

Dean swallowed thickly and turned around slowly. He was pretty sure he was going to throw up when he found himself eye to eye with the blue eyed teenager, who was honestly standing way to close to be consider proper anyway. Dean took a step back, his face turning bright red. He stuttered over a couple words unable to meet that bright blue gaze, “I… Uh…” 

Thankfully, Sam came around the corner then looking for Dean. “Hey Dean! There you are. I needed some help figuring out which looks be…” Sam was cut off though when Dean suddenly grabbed his arm after shoving the panties into the other teens chest. “Gotta go Sam, forgot I left the stove on” Dean said making a quick escape and leaving the teenager standing there holding a pair of soft pink lacy panties and his eyes watching Dean run away, face still red. 

“Uh Dean what the hell? We had pizza for dinner the stove was never on” said Sam when they reach the impala. Dean just got in and slammed the door not saying anything. “Come on we’re going to another store. I didn't like that one” he said ignoring Sams question. Sam knew something was up but he also knew his brother well enough not to say anything. For the rest of the evening, Dean couldn't stop thinking about those blue eyes.

.............................

The weekend went by quickly for Dean. Sam kept shooting him funny looks and tried to ask about Friday night again but Dean would just shut his bedroom door or turn his music up louder. Other then avoiding Sams pestering, Dean occupied his time by watching Doctor Who in his room and fan-boying (because he wasn't a girl) over it with his best friend Charlie, who was the only person that knew he watched the show. She was also the only person Dean had thought about talking to about his… strange kink due to the fact Charlie was a lesbian. But he was too much of a chicken to bring it up to her. 

At night though, Dean would lay awake still hearing Castiel’s voice ringing in his ears. On Sunday night Sam went over to a friends house for dinner and to study leaving Dean alone in the house. Once Dean was sure Sam was gone he slipped into his room and slowly slide the box containing his panties out. He picked his favorite pair, a light blue, with a lace lining that looked perfect on him. Dean slide the underwear on after removing his boxers. The material slide over his skin easily and after just a little readjusting sat perfectly around Dean’s butt and balls. A slight sigh came out of Dean’s parted lips as he admired himself in the mirror smirking. That’s when Castiel decided to push his way into Deans thoughts and Dean could feel arousal shoot down his stomach as he thought about Castiel coming up behind him and giving his ass a light squeeze, whispering into Deans ear how sexy he looked.

A low groan escaped Dean’s lips as he palmed himself through the soft material. His hard length was quite obvious now, straining in the material, barely being held in. Laying down on his bed, Dean spread his legs and rubbed himself through the material. Blue eyes floated through his vision and that rough sex god voice echoed in his ears as Dean reached over to his bed side and pulled out his lube. He’d only been brave enough to try this once or twice but right now he was suddenly feeling the need to have something inside of him. Pulling the material aside but not removing it, Dean circled his entrance with one finger before slowly pushing in. His head fell back and his mouth was opened in an “O” shape at the amazing feeling of being filled and stretched took over. Slowly Dean worked himself open, low moans and grunts leaving his mouth and the occasional slip of Cas’s name. Eventually he had three fingers in himself, the most he’s ever had, and fuck did it feel amazing. The panties were still on, and by now they were digging into Dean’s skin still keeping his length trapped. For some reason Dean can’t bring himself to remove them, instead he took his other hand and rubbed himself through the material. A light friction was caused and it only took a few more pumps and thrusts before Dean was coming, All while moaning out Castiel’s name and imaging it was him inside of Dean.

Now exhausted and out of breath, Dean collapsed back against his bed coming down from his orgasm. Once his breath was caught, Dean looked down and frowned at the now soaking panties. Shit he was going to have to clean them.

Quickly Dean got up and removed the underwear. He hopped into the shower to clean himself and then ran the material under the warm water, gently working the mess out of them. Once he finished, Dean looked around wondering where the hell was was supposed to hang them so they can dry without Sam finding them since they shared a bathroom. Dean figured his closest will have to do since Sam doesn't come into his bedroom anyway.

After hanging the wet panties up to dry, Dean pulled on boxers and collapsed back into his bed. He stared up at the ceiling feeling slightly sore and completely exhausted. His last thoughts before he fell asleep were that he was completely and totally fucked, Cas was going to be the death of him .

**Notes for the Chapter:**

> So that is it for now! I am already working on the next part so please tell me if you would like more! Also if anyone would like to beta this for me (I know I need it) feel free to shoot me a message :) .


	2. Chapter 2

**Summary for the Chapter:**

> And the next thing Dean knew he was spilling coffee on to the front of some strangers shoes.

Monday dawned dark and gloomy for Dean Winchester both literally and figuratively. Castiel was still all he could think about and the panties hanging in his closest were a reminder that it wasn't something he was getting over any time soon. Thankfully Dean didn't have to take Sam to school today leaving time for himself this morning. Slowly, Dean rolled himself out of bed and dragged himself to his bathroom where he took a shower just letting the warm water sooth him. He tried not to let any images of bright blue eyes pop up into his vision but it proved to be more of a challenge the Dean realized leading to him having to take the rest of his shower under cold water to keep from getting aroused. After his not so pleasant shower, Dean made his way to the kitchen only to find that they were in fact out of coffee. "Fuck" he mumbled under his breath running a hand through his still wet hair. He needed his coffee fix dammit. With a low sigh, the teenager walked back to his room and grabbed his coat and car keys accepting the fact he was just going to have to stop and pick up some ridiculously expansive coffee from some stupid cafe probably full of rich pricks with their overly fancy coffees. Yeah, today was going to be just peachy. 

Dean stepped out of the house into the light drizzle that didn't look like it was going to stop any time soon. In fact the clouds looked like they were just waiting for the opportunity to open up and drown anything that had the unluckiness to be stuck under them. This definitely wasn't helping his already shitty mood. Shoving his hands in his pockets, the teen ducked his head and walked swiftly to his car, opening up the impala's door and jumping in as fast as he could, he really hated getting the seats of his baby wet. Dean started the car and was about to back out of the drive way when he notices that he was practically running on empty, his gas needle hovering just above the red. Well shit now he was going to have to pay for gas too with his slowly dwindling amount of money. He huffed, accepting the fact he was going to have to pick up extra hours now, and started backing out of the driveway seriously debating whether he should just give up on today and go back to bed, but he knew he couldn't do that, he couldn't let Sammy down. So with much effort Dean drove himself to the nearest gas station, filled his baby up, (seriously $3.50 for a gallon of gas), and then heads out to find a coffee shop. He passed a Starbucks with a line so long people were almost out the door, uh ya no way. So he kept driving until he spots a small little shop squished between some electronic shop and what looked like a candy store. "What the hell" Dean thought to himself as he parked the Impala outside the little Cafe and made his way inside. 

A nice surprise consisting of a warm friendly atmosphere and the sweet aroma of coffee without all that fancy shit greeted him. "Fuck it smells amazing in here" Dean said not even thinking about the fact he just said that out loud, in an empty shop with only the person behind the counter. The man looked up with a smirk, he was a short little thing with blonde hair and honey colored eyes. "Well thanks there kiddo, I'll take that as a compliment," he said while he sucks on a lollipop, "so what can I get you today hot stuff?" the man, Gabriel, as his name tag read, asked with a wink. Warmth rose on Dean's neck and cheeks as he blushed slightly at the servers words. "Uh..." he shook his head and quickly regained his cool. Seriously, Winchesters do not get flustered. "Ya, i'll have a coffee with sugar and no creme please" Dean said before turning a little and eyeing the sweet pastries sitting in a glass case by the register. He couldn't help when his mouth started watering and he licked his lips. "and uh, i'll have one of those muffins" he says pointing to the delicious looking thing with what looks like cinnamon sugar covering it. Gabriel nodded his approval, "Good choice, I gotta say it is definitely one of my favorites, who knew my baby brother would be such a god in the kitchen." Gabriel said chuckling. Dean just nodded his head not sure what he was suppose to say to that. The man quickly rang up Dean's order and slid the piping hot coffee and muffin over to him. "That'll be $5.46" he said and Dean groaned. "At least it's cheaper then Starbucks" he mumbled quietly but apparently not quietly enough. The blonde man laughed and just shook his head making Dean feel a bit like an idiot. 

Dean sighed and pulled the coffee close taking a deep whiff. Maybe his day was finally looking up, but then of course life had to go and prove him wrong. "Hey Gabriel! I'm heading off to school now" a voice calls out that makes Dean's back go straight and his eyes go wide. He knew that voice, no fuck, it can't be. Oh but it can be because coming out from the back of the little shop was no other then Castiel. As quick as he could, Dean grabbed his food and turned to leave not having realized someone else had walked into the store behind him. This led to the poor stranger having Dean's hot coffee spilled all across his feet, "Shit shit shit, I'm so sorry!" Dean says stepping back to take in the stranger. Behind him Dean heard someone gasp and laughter. His face turned bright red and as much as he wanted to turn around to grab some napkins to help the man he couldn't bring himself to look at the boy who had caught him looking at women's panties three days ago. So Dean did the only thing he could think of making himself feel like a complete ass in the process. "I'm so sorry!" he apologized again before making a run for the door and to the impala. He hoped in and sunk down in the seat noticing how Gabriel was still laughing and Castiel had run around the counter to help the customer, sending confused looks out the door. Dean really hoped Castiel hadn't recognized him. 

The rest of the day went by just as shitty for Dean. After loosing his coffee, he ended up falling asleep during his second period. Next during math there was a pop quiz which he definitely failed, plus Dean didn't have enough money for lunch and dinner leaving him to smooch food from his friends. Then on the way home some guy was too busy talking on the phone and rear ended Dean leaving a nice dent in the impala's bumper. It took everything he had not to rip the guy a new one and smash his phone to pieces. He went to work after that hoping at least that would be better. Bobby could tell Dean was in an awful mood and tried to ask only to get a glare from Dean which earned him time in the office with Bobby saying that if he was in such a bad mood no way was he working with tools. 

Finally, after probably one of the shittiest days he's ever had Dean was finally back at home listening to his brother go on and on about some subject they are learning about in history. Dean crawled into bed later that night and stared up at the ceiling and prayed that the rest of his week would be better. 

But Dean wasn't that lucky and the rest of the week went by much like that Monday. At least he didn't have another run in with Castiel, well that held true until Sunday came around.

**Notes for the Chapter:**

> Hope y'all enjoyed this installment. Please comment or just leave kudos. Once again if any one like to beta this or just leave some tips feel free! :) Also I know my tenses still suck, which is why I need a beta! ahah. Thanks for reading!


	3. Chapter 3

**Summary for the Chapter:**

> Dean has some nice fantasies and finds himself in another uncomfortable situation. Also Sam isn't sure what to think any more.

**Notes for the Chapter:**

> Hi! So just so everyone is aware, the last chapter ended talking about Sunday but this chapter starts on Saturday night and then goes to the scene that was hinted at, at the end of last chapter. I just don't want any confusion. There is a sex scene in this just so y'all know.Also this is still un-betaed so all mistakes are my own, if any one would like to beta just send me a message and I will love you forever. Enjoy.

Saturday night had been another night of Dean home alone while his younger brother was out having a better social life then him. However the night wasn't completely a drag and Dean once again found himself wearing another pair of panties. This time a soft almost completely lace pair, with cheetah print cloth over only the crotch area and the rest being lace. He checked his ass out in the mirror, grinning at how nice the black lace made it look, so round and fuckable.

Dean swallowed thickly and moved away from the mirror, quickly going towards his bed. He wasn't supposed to be having these kind of thoughts, dammit. Dean was straight... yet Castiel still flirted around in the back of his mind with a smirk on his face saying "Are you sure?" 

With a groan, the teen fell back on to his bed still wearing the underwear. He shifted a little causing him to moan at the feeling of the material stretching and pulling over his balls. Slowly his length started to harden and Dean finally gave into the day dreams like he'd wanted to all week. The boy leaned back on his bed, hands traveling down his body as he closed his eyes and thought of Cas.

Blue eyes danced across his vision as an image of the coffee ship came into mind with Cas wearing nothing more then an apron. Dean was spread out across the counter top, his ass presented in the air surrounded by pink lace.

"Look at you," Castiel purred as his hand traveled up over Dean's ass giving it a light smack, "all flushed and spread out wanting my touch, my cock." Castiel pulled Dean's earlobe between his teeth and gave it a light tug causing the man under him to gasp a little. Then he took his hand and kneaded the the mounds of flesh that made up the boys beautiful ass. 

Dean heard an almost animal like sound escape his mouth taking himself by surprise, "yes baby, please!!" he begged, wiggling his ass in temptation for the blue eyed man behind him. 

Castiel smirked and reached behind his back tugging the knot loose on the apron and slowly sliding it off from around his neck. It fell to the floor in a puddle of white cloth and a foot kicked it aside. A now naked Cas stepped up behind Dean and pulled the panties to the side. Dean looked behind himself and almost came right there and then from the sight of Castiel's hard length curling up towards his stomach, precome breading at the tip. It took everything the green eyed man had not to turn around and swallow the long length all the way down. 

Suddenly a whine escaped the back of the teens throat as the other circled a finger around his puckered, waiting entrance, before slowly pushing in. 

"Does that feel good Dean?" Cas whispered into his ear, leaning over his body. A moan was the only response Cas received so he started to move his finger in and out. By the time Castiel had three fingers in him, stretching him open nice and wide, Dean was almost completely gone, rutting against the counter to try and get some friction on his aching cock. 

A door slammed shut pulling Dean out of his fantasy with a loud gasp and come spewing across his stomach painting him white. "Fuck" he muttered. 

"Dean! I'm home!" Sam called out, walking down the hall towards Dean's room not giving the older brother anytime to enjoy his post orgasmic haze. Dean jumped up quickly grabbing tissues to wipe off his stomach as he pulled on a pair of sweats covering up the panties he was still wearing. 

Sam walked in Dean's room after a quick knock on the door, "Hey you okay..." Sam froze, his face pulling up into one of his famous bitch faces when the smell of sex hit him and he took in the sight of his flushed, disheveled brother. "oh eww, Dean gross!" Sam complained moving back out of the room. However before he did his eyes landed on the box of panties sitting on Dean's desk, a pair hanging over the edge. The younger boys eyes went wide and he quickly closed the door. Sam may be young but he wasn't naive and unless Dean was hiding someone in his small room, which Sam doubted, it meant there was more to his brother then met the eye. It made the boy a little sad though, he thought he knew everything about Dean, that they told each other everything. But it seemed like Dean was too scared to tell Sam about this. Maybe he really didn't know his brother at all. 

Sam made his way to his room where he plopped down on his bed with a sigh. He wasn't going to say anything though, Dean would tell him when he was ready. It was just that Sam wished Dean realized that it didn't matter if he liked to strut around in ladies underwear or that he was possibly gay, it wouldn't change the fact that Dean will always be his older brother. 

Dean stood in his room staring at the now closed door. It wasn't that his brother knew he masturbated that bothered him, it was that Dean is pretty sure his brother saw the box of his most secret possessions sitting on the desk. His head fell into his hands as he tried not to have a panic attack. What was he going to do? What was Sam going to think? What was he going to say? 

The room felt chilled now against Dean's heated skin. A pathetic sigh left him as he moved over to put away the box after removing the pair he was still wearing. The lid closed over them cutting off that part of Dean as he slide the box back under his bed. 

He shivered a little and pulled on a pair of boxers not finding the loose cotton material nearly as comfortable as the silk of the underwear. The sheets of his bed were warm and welcoming as he climbed between them and curled up in a ball holding his pillow tightly. Dean closed his eyes and hummed quietly to himself trying to not think about the events of tonight. Eventually he did drift off to sleep not waking again till morning. 

...........................................

Sunday morning went like almost every Sunday before that. When Dean walked out of his bedroom, Sam was already up making breakfast like he always did on Sunday. Neither one of them mentioned the previous night and they fell into a comfortable silence that had always been something the brothers did easily. 

"Hey Dean, I know we don't have much money and you're working your ass off but uh.. Man I kinda really need some more socks" Sam said blushing and acting like the subject of socks was just the most embarrassing thing. For some reason Dean found this hilarious and broke out in a hearty laughter. 

"Don't worry Sammy, I will run by the store and pick you up some, I have to go out anyway and get my pay check from Bobby." Dean said sitting down at the table with a bowl of cereal and a grin on his face. Sam flicked some eggs at him. 

"You're a jerk" he mumbled.

Dean only smirked more, "I love you too bitch."

Sam rolled his eyes but other then that the morning was spent in silence as Sam mused over his homework and Dean thought about how he should probably do his own homework. Around noon Dean grabbed his keys ready to head out. "Hey Sam, I'm going to go ahead and head out. I will buy us some lunch on the way home." 

Sam lifted his head being shaken out of his homework trance that made him forget about the outside world. "Uh okay cool, anything is fine!" he shouted back before going back to concentrating on the numbers in front of him.

With a shrug and a small huff Dean made his way out to the impala. He started her up and headed to the store that Castiel worked at. However Dean knew that Castiel didn't normally work Sunday's and so he was hoping this still held true and he wouldn't see the beautiful teen. A few minutes later, he was walking through the stores doors, his shoulders tense and waiting for that blue gaze to meet him. Instead there was a guy Dean had seen once or twice asleep at the register and a girl with bright red hair walking through the aisles taking inventory while chomping away on a piece of gum. Both of them seemed completely oblivious to their surroundings. A relieved breath left Dean as he walked towards the area of the store that held the socks. 

He stood there for a little bit contemplating whether or not to get Sam a pair of tall tube socks with clown faces on them. The reaction he knew he would get from Sam was enough to send Dean into a small fit of laughter. He chuckled again and decided that as funny as that was he couldn't waist the money. So Dean grabbed a couple packages of socks and was making his way to the registers when he noticed the apparel aisle. The urge to go and look at what was new was so strong he couldn't resist it. He paused and thought about it, the store was basically empty, there was no Castiel around, the workers were too busy sleeping or caught up in their own world to notice. With a sly grin, Dean slunk down the aisle and stood in front of the women's underwear with a shy grin. His eyes roamed over all the different colors and patterns, the different materials and lace. With a happy sigh he picked out a couple different pairs, one of them being a fiery red pair that made him feel so naughty just holding. 

Dean glanced around again just to make sure he was alone before quickly walking back towards the dressing rooms. You weren't technically allowed to try on underwear due to sanitary reasons but Dean wanted to hold them up and see what he thought they might look like on him. He slipped inside one of the many empty stalls and locked the door. The button of his jeans popped open and the zipper slide down as he pushed them down around his ankles. Then he picked up the first pair, a kind of peach colored pair and held it up to his hips. The color really didn't work for him so he dropped the pair and reached for the next. This one was green, a pale green with a lace trimming and a little bow on them which Dean loved. The color didn't look bad on him and it actually kind of brought out his eyes. Maybe he would get them but now it was time for the red pair. Their was no lace on them but they were cut a little different from the other pairs. They also had bow on them. Dean grinned wide as he held them up, the color looked amazing on him and the material was perfect. Excited, he pulled on his pants and grabbed the panties into his hands, the socks tucked under his arm. 

Dean left the dressing room, a grin on his face. He thought he was still alone but then probably the worst possible thing to ever have happened to Dean ran into him as he was walking out of the dressing rooms. "Fuck" Dean said stumbling backwards. 

"I'm so sorry sir!" the worker exclaimed looking up from where he had been picking up clothes that other people had left lying around. Dean felt his stomach plummet and his heart rate accelerate as he found himself looking into a pair of very familiar eyes. It was Castiel, it just had to be Castiel. 

Castiel looked just as surprised to see Dean as Dean was to see him accept he regained himself quicker. A small smirk came on to his face as he recognized the man in front of him from their past two meetings. The workers eyes drifted down to the apparel being tightly clutched in Deans hands and he raised an eyebrow. Dean's face was bright red at this point and he was stuttering trying to come up with an explanation and then make a run for it. 

That is when Castiel took him completely by surprise. A playful smirk light up the boys face as he shifted the cloths he was holding to one arm. He reached forward and pulled the red pair of panties out of Dean's tight grasp. Holding them up with one finger, the man looked between them and Dean who was still red as a tomato. "Mmm this is definitely your color. Get these one. I like them" Castiel says with a smirk and wink placing the panties back in Dean's hand. 

Dean was pretty sure his mouth was hanging wide open and he might even be slightly aroused. Castiel removed the other two pairs from his now limp hands and turned to walk away. He paused though and looked over his shoulder at Dean, his eyes still playful and a smirk still on his face, "By the way, you're pretty cute when you're all flustered and red." With that the boy was gone off to put clothing back where they belong. 

It probably took Dean a good five minutes before he was able to breath properly again. He walked to the front of the store in a sort of haze and bought the socks as well as the red underwear. The man at the register didn't even blink an eye at them and Dean left the store feeling confused about what the hell just happened. 

He sits in his car, starring at out the window for awhile unable to convince himself to drive anywhere. It slowly started to process through his mind what the fuck just happened. 

Holy fuck, Cas thought he was cute!!

**Notes for the Chapter:**

> I would like to thank Naamah for giving me the idea for the dressing room! Also I am sorry for the terrible smut ahah. Really if y'all have any suggestions or pointers I would love to hear them as long as they're said nicely. Thanks for reading! There is more to come.


	4. Chapter 4

**Summary for the Chapter:**

> Dean starts to learn that maybe being... him isn't such a bad thing.

**Notes for the Chapter:**

> Hey guys, wow so I have gotten way more kudos then I ever thought I would on this story so thank you guys so much! You guys are awesome seriously. Well here is the next installment. This chapter is short because it's just a lot a dialogue and Dean...  
> Hope y'all enjoy this chapter!! Please comment! Seriously! I love them so much <3 
> 
> Warning there is some homophobic teasing in this chapter and Dean has a lot of self worth issues. Also Christian and Dean aren't related in this fic.

Monday morning Dean got to school early to seek out Charlie. After the events yesterday, Dean desperately needed someone to talk to and she was the only person he knew wouldn't judge him. He spied some of his teammates from the baseball team in the middle of the courtyard. They were spread out on the grass, tossing balls around, and flirting with girls. It was probably where they normally hung out in the morning, not that Dean knew as he usually got there late either from dropping Sam off or just cause he was sleeping in. He grimaced a little, staying on the out skirts of the courtyard that he had no choice but to cross. The last thing he wanted to do was to deal with Alistair and his crew today. You could say that their baseball team was divided into two parts. The part that followed Dean, the team captain, and then the assholes who followed Alistair and basically tried to run the school. Dean wasn't that lucky though and one of his least favorite teammates spotted him as he was almost into the other building. 

"Yo! Dean! What are you here so early!" Gordon yelled out nudging his friends around him to get their attention. They all stopped, their attention turning to their captain who they hardly ever saw. "Sneaking around to see some girl you're hiding from us?" Dean huffed and rolled his eyes, he really didn't want to deal with their crap this morning but he knew if he didn't at least acknowledge them he would get even more crap later. So he hooked his bag a little farther over his shoulder and trudged through the damp grass towards his teammates.  

"Hey guys," He said forcing a smile and trying to look natural and comfortable, like he totally wanted to be there and didn't have some where better to be. "Whats up?" 

Christian snorted from his position on the grass, some girl Dean didn't recognize tucked against his side. "What's up is our oh so popular captain seems to be avoiding his teammates." Dean huffed a little thinking to himself, "Yeah I wonder why," but he keeps his mouth closed allowing Christian to continue. "The only time we ever see you is when we're at practice and even then you run off as soon as it's over. " 

Another player spoke up and Dean had to suppress an eye roll, " Yeah! You got yourself some secret girlfriend or something?"

"Oooo or maybe we have ourselves a faggot!!" Christian spat out as he leaned forward slightly, upsetting the girl by his side. It took everything Dean had not to punch the living day lights out of the little prick. He gritted his teeth together and rolled his eyes for real this time.

"You guys are fucking stupid." Dean said as he ran a hand through his hair and glanced around at the other team mates. He noted Alistair wasn't actually here this morning and that was actually a bit of a relief. "If anyone here is a faggot it's Gordon." He said, smirking at the younger man, "Do I need to remind y'all about last years end of the year party?" Gordon turned bright red and rubbed the back of his neck as the team hooted and hollered with laughter around them. Dean just smirked.

"Up yours Winchester" Gordon growled out at him, flicking him off.

"No I am pretty sure it went up yours, and please spare us the details," said Dean holding his hands up and backing away slightly. He was going to sneak off while the team was busy laughing. But he paused, "Oh and Christian, hun," Dean said gingerly like he was talking to a scared animal, "Some of us actually have to work to make money, we don't have everything handed to us on a silver platter by mommy and daddy. I don't wanna scare you but it's a bitch of a world out there, sometimes you gotta get your hands a little dirty." Christian turned slightly red and his teammates snickered around them, "Oh and hey at least I can buy my own condoms."

With that Dean spun on his heal and stalked of to find Charlie leaving the team behind him as they laughed and teased Christian about the time he had to ask his dad for condoms.

A quick glance down at his watch showed Dean that he now only had about ten minutes until first bell rang. With a sigh, he trudged his way through the growing throng of people to find Charlie who he knew would be at the library geeking out on the computers with her friend Kevin.  

The cool, dusty air of the library greeted him as he walked through the doors, spotting the familiar flare of red hair that told him where Charlie was almost right away. Dean maneuvered his way through the tables of people studying and the book shelves of barely touched books until he reached the two. "Hey guys," he said dropping his back on the ground next to Charlie's chair who was currently completely absorbed in whatever game she was playing. Technically school computers blocked all of theses things but Charlie being well Charlie hacked the system and now you can do anything you wanted on these computers and no one had a clue who did it. 

Charlie held up a finger to signal one moment making Dean rolled his eyes but he smiled anyway leaning over her shoulder to see what she was playing. He didn't recognize it. "Hey Dean" said Kevin from his place beside her, a SAT book propped up against another computer in front of him. This man was a genius honestly and Dean had no clue why he spent so much time studying anyway. There was no way he wasn't going to get a perfect score. 

"Hey Kevin" Dean replied sending him a small smile. 

"Dammit!" Charlie almost shouted slamming her hand down as the words "Game Over" popped up on the screen, "I had almost beaten my high score." She turned to Dean a pout on her face. He just smiled and shook his head. 

"You'll get them next time" he said affectionately but then he paused for moment looking down at the ground, "Hey Charlie, I..." Dean blushed suddenly feeling awkward. Fuck what was he supposed to say? That he might be into guys? That he liked to wear girls under wear? That he's so fucked up. He glanced at Kevin who looked up from his studies realizing that the atmosphere had suddenly changed. 

"Whelp I am going to take that as my cue to leave. I'll see you later Charlie to help you with your computer." Kevin said quickly gathering his things and scooting out of there. That boy hated awkward moments more then Dean did. 

Charlie frowned and pulled Dean down into the now vacant seat, "Alright what's going on in that noggin of yours?" 

He sighed and pulled his bag into his lap resting his chin on it. Dean suddenly felt super aware of everything, the library felt too loud, he could hear the girls giggling a couple tables over, and the librarian shushing people. The room was hot and stuffy and sweat was starting to roll down the back of his neck. "Uh can we go somewhere else?" he asked desperately needing to get away. Suddenly he shot up from his chair. God it felt like everyone was watching him and he hadn't even said anything yet. They couldn't know! He hadn't told any one! There wasn't anything wrong with him! He wanted to shout this out at everyone.

Charlie's frown deepened, concerned for her best friend who looked like he was starting to have a panic attack. She quickly hooked her bag over her shoulder and grabbed his hand, pulling him out of the library and down the hallway to the computer lab no one used anymore and was just full of broken lap tops. The door was kept locked but Charlie had more then a few secrets and she quickly picked the lock and pulled Dean inside, closing the door behind them. "Alright dude, just breath." She said sitting him down in a dusty chair.  

The feel of Charlie's hand in his helped to ground him a little and Dean realized his breathing was coming out ragged and his chest hurt. He wasn't sure where Charlie had dragged him off to but it was quiet and he could tell they were alone. His bag slide to the ground with an echoing thump and his head fell between his legs as Dean slowly began to regain control of himself again. 

After a moment he sat up and ran a hand through his hair. Charlie was leaning against a table, eyeing him wearily. "Alright you wanna talk about it now? Or not ya know. Just don't do that again. Please cause holy hell that was kinda scary. I thought you were going to pass out." 

Dean made a face and shakes his head, "No, I'm fine I'm sorry I just... There is something I really need to talk to you about and you're the only person I feel won't freak out on me" he said starring down at his hands. 

The red head chuckled a little and pushed off from the table, "Alright go ahead." she said crossing her legs and settling on the floor in front of Dean. 

He blushed red and couldn't bring himself to look at her. Instead he looked around the room taking in the broken computers, the way the sun barely filtered through the dusty blinds. Dean's stomach felt like a million bricks were in it and his throat was the Sahara desert. The teen swallowed thickly, "I like... " he coughs, "Fuck I don't know if I can do this" he mumbles." 

Charlie sighed, "Dean seriously, for once in your life don't make me beat it out of you. Just tell me I promise I won't judge"

He nodded and clenched his hands together, "I... I think I'm gay... I like to wear women's underwear" he barely managed to choke the last part out squeezing his eyes closed. 

There was a pregnant pauses before Dean finally opened his eyes to look at Charlie who was just sitting there staring at him. Finally she rolled her eyes and blew a raspberry, "Is that it? Seriously?" She asked giving Dean a look.

Dean's pretty sure his heart stopped for a moment and then all his breath came out at once, "What the hell do you mean is that it?"

Charlie laughed, leaning forward so her head hit Dean's knees, "Come on Dean. I am your best friend, your best friend who happens to be gay. You honestly think I didn't know?"

He blushed brighter and looked away rubbing the back of his neck, "Uh well yeah..." he swallowed again and a small smile came on to his face, "So you don't care?"

"Oh you're kidding me right? You seriously thought I would care? Hell no you idiot" she said shoving his legs, "I also know you have a thing for the boy who works at Jenny's clothing store. If you really think I didn't notice all the times you would go into that store. At least once a week? No one buys clothes that much Dean. Or how whenever anyone would mention being gay or make a gay joke you would go tense. Come on, I'm your best friend, I am suppose to know these things. What bothers me is why you thought you couldn't tell me" she said placing her chin on his knees.

Dean sighed and ran another hand through his hair, it was quickly becoming a nervous habit of his, "I was scared... I am scared" he whispered out, "These people will tear me apart if they found out. Oh god Charlie just think what would happen to me if Alistair and his crew found out. It would be the end of me. My life at school is good, everyone respects me, I'm captain of the baseball team, all the girls want me and all the boys want to be like me. If it came out that I like guys, _that I like to wear girls underwear_ , it would be the end of me Charlie and you know it." His breathing was picking up again at the thought of what could happen to him. He already was a disappointment to his father, he couldn't disappoint the rest of his friends, and oh god what would Sam think of him? Fuck, he was such a screw up, he couldn't even like the right sex. 

A smack to the back of the head brought Dean back to the present moment, "Alright stop whatever you were thinking and also shut up. Do you seriously care that much about what these fuckers think? Alistair is a piece of crap and so are all of his followers. The whole school knows that. Also I am openly gay and come on Dean have you ever once seen me being bullied. No ones going to care. As long as you don't give them a reason to." Charlie smiled and pulled him down for an awkward hug, "Besides I think it's kinda hot that you like to wear girls underwear and I don't even roll that way" 

Dean laughed and hugged her back tightly tears welling up on the edge of his eyes. Just knowing she had his back took a huge weight off his back and yeah maybe she was right. Maybe being gay wasn't such a bad thing. He pulled back wiping his eyes and laughing a little, "Thanks Charlie, you've uh given me a lot to think about." 

She smirked and nudged his shoulder, "I'm awesome I know, also if Alistair does try to mess with you, don't worry, we gottcha back." Dean rolled his and smiled.

"There is one other thing... Cas kinda uh... caught me... trying on panties at the store." he paused, "oh uh Cas is the boy I have a crush on." 

Charlie fell back on to the ground laughing, "Oh.. oh god I wish I had been there to see that." Dean glared at her, "Hey at least you finally talked to him." 

"Well that was actually the third time we had run into each other..." Dean trailed off with a blush. Charlie grinned, "alright that's it I am coming over for pizza and you are telling me everything! But right now I am feeling all warn out from all these emotions man." she faked a big yawn and Dean kicked her lightly and she swatted his foot. 

"Come on asshat we're going to be late to class," Dean said standing up and hooking his bag over his shoulder, already he felt ten times better even though he had a lot to still sort out. Plus he was excited now to get to tell Charlie all about Cas. Maybe she would know what the hell he was supposed to do. 

The two made their way out of the computer lab, Charlie making sure to lock up behind them, and headed off to class. 

Dean never would have allowed Charlie to come over that evening if he knew what was going to happen. 

**Notes for the Chapter:**

> So this chapter was actually longer then I thought it would be :D 
> 
> However I am not very happy with it... 
> 
> The next chapter Charlie pulls some strings, and Castiel and Dean have their first real conversation without Dean running off.
> 
> I also have a new story called It Always Happens at Midnight that I would love for you guys to check out :)


	5. Chapter 5

**Summary for the Chapter:**

> It finally happens.

**Notes for the Chapter:**

> Oh my gosh I'm so sorry this took so long. First it was finals, and then I just couldn't get time to sit down to write, then my laptop broke. And yeah. Also this is the longest chapter I've ever written! :D I'm not too proud of it to be honest but at the same time I like what I did with it. I just feel my writing could have been ten times better. But tell me what you think! I also think I'm only gonna have a couple more chapters and then end it. Unless there is something else you would like to see? If there is please tell me!!!
> 
> Also follow me on tumblr at casorpiedeanwinchester

That evening Dean sat on the couch waiting for Charlie to show up so they could have their big girly discussion, or whatever she was planning. Right now she was with Kevin and Dean was seriously wondering what was taking so long. He was idly flipping through channels on the TV not really paying attention to anything, his mind still too distracted by the idea of trying to get up the fucking courage to actually talk to Castiel. Lucky for Dean, Sam had decided to go over to a friend’s house for the evening leaving the house blissfully empty until Charlie arrived.

Around six o’clock Charlie still hadn’t arrived and Dean was starting to get really antsy as well as hungry. His stomach let out a loud growl to confirm that fact, so Dean reached over and grabbed his phone, typing out a quick message to Charlie.

To Charlie: Yo, where are you? I’m about to order the pizza without you.

It was only a couple minutes later that Dean received a reply making him roll his eyes because way to be busy Charlie,

From Charlie: I was actually thinking we could go out to eat? You could use some fresh air that doesn’t involve stalking your blue eyed man crush :D

Dean just huffed and was about to reply when his phone pinged again signaling another message.

From Charlie: My treattttt!?!?!?!

Well damn, it wasn’t like Dean could say no to free food. So with a groan, he rolled off the couch and pushed himself to his feet, making his way over to the door to grab his keys.

To Charlie: Alright you win… where are we meeting? And it better involve lots of meat!

Dean locked his phone and slide it into his pocket while he waited for Charlie’s reply which was almost instant making the teen chuckle a little as he pulled his phone back out and quickly read the message.

From Charlie: Meet at the diner down the street from my place, the ones with the really good burgers. Oh and don’t worry they’re will be plenty of meat ;D

Dean was really going to beat himself up later for not reading into that text but at the moment his stomach was the one thinking for him and all it heard was really good burgers.

He opened the front door noting how the weather was finally starting to cool off. Leaves crunched under his feet as he hurried to the impala glad he had left his leather jacket in there. The drive to the diner didn’t take too long, although dealing with rush hour traffic was always a real bitch.

Finally, Dean pulled into the diner finding a spot off to the side where his baby would be safe from idiot drivers who didn’t know how to park. He walked into the diner and spotted Charlie’s red hair almost right away, plus it was hard to miss her beaming smile and booming laugh. That’s when Dean realized that there was someone sitting across from her, someone with familiar ruffled brunette hair, and someone who Dean was pretty sure he would recognize anywhere. His stomach dropped and his face paled as his feet carried him forward against his will.

Charlie spotted Dean and ignored his pale face as she called out, “Dean!” while waving him the rest of the way over.

The man sitting across from Charlie turned and looked at him, a smirk on his face. Dean’s pretty sure that if he’s stomach wasn’t so empty the contents of it would have been on the floor at this point.

“Oh hey Dean,” Charlie said with an evil grin on her face, “I think I forgot to mention earlier that Kevin and Castiel were good friends. They go to the same church or something.” She picked up a fork, waving it at Castiel and then started playing with it, “turns out on Monday’s they normally meet for some studying group thingy. So I decided to invite them along to dinner. Kevin couldn’t come but I hope you don’t mind that Castiel here tagged along,” the evil smirk was still on her face as she set the fork down and smiled up at Dean trying to look all innocent.

“Oh… how convenient,” Dean choked out standing there awkwardly at the end of the table, feeling hot under that blue gaze. “You know Charlie, I’m actually not feeling that hungry anymore. I think I might be coming down with something. I should just leave and you two can enjoy your meal” he said already slowly trying to back away. How could Charlie do this to him? There was no way in hell he was ready to actually talk to Castiel yet. Besides, the guy probably thought Dean was a joke, and judging by how attractive he was (and knowing Dean’s luck), Cas was probably already completely off the market. However his stomach chose that moment to speak up for him, making a loud rumbling noise and proving to everyone around that Dean was in fact quite hungry. He didn’t even dare look at Castiel, who was now chuckling softly behind his hand, eyes still on Dean.

“Oh really? Because I heard pie is the special dessert for the night,” Charlie said in a sing - song voice, a grin on a face because she knew she had won.

The green eyed teen let out a small groan before plopping into the booth beside Charlie. He glared at her from the side of his eyes, trying not to make any eye contact with the gorgeous man across from him. “I hate you,” he mumbled under his breath at her while staring awkwardly down at the wooden table top in front of him.

Castiel was just sitting there watching Dean with an amused smile on his face. He couldn’t believe that he could have such an effect on someone, especially someone as beautiful as Dean. He was pleased with himself that he had let Charlie talk him into the dinner. Although he really wished they would just include him in the conversation already.

“You’ll thank me later,” Charlie whispered back, elbowing Dean in the side, making him grimace.

Dean was pretty sure he was going to die before that happened. He could feel the sweat rolling down the back of his neck even though the air in the room was cold. Everything just felt awkward and stiff, the walls of the room too close. Dean swallowed thickly, staring down at his hands on the table, picking at a piece of wood. What was he supposed to say? What was he supposed to do? It wasn’t like he could just come out and be like, “ Oh hey there, I think you’re fucking gorgeous and I’ve been stalking you at work for a couple months now, want to go out with me?” Yeah the guy called him cute but that didn’t mean anything. He could think Dean was a total freak for being into girls underwear. Dean’s chest feels too tight and he’s pretty sure his breathing picks up. He was about to have a full blown panic attack until Charlie clears her throat.

“So do you two know each other by any chance?” She asked them, eyeing Dean a little wearily. He just huffed and rolled his eyes, knowing that Charlie already knew the answer to that question.

Castiel finally spoke up, “Oh we’ve run into each other a time or two. But they were mostly cases of hit and run,” he said a playful smirk on his face turning Dean a bright shade of red as he recalls the coffee shop incident. He just buries his face in his hands, wishing the world would just open up at this point and suck him in.

Charlie leans forward resting her chin on the palm of her hand, “Oh really, tell me more,” She said, her eyes playful. Dean was so going to kill her.

The blue eyed god chuckled, “Well mostly I’ve just seen him around the store I work at a lot. He seems to have a thing for women’s apparel. There was also the incident at my brother’s cafe.”

Dean could feel himself blush even brighter, glad that he had already told Charlie about the pantie things. He picked his head up slightly to look at Castiel and is relieved to see the man smiling and nothing more in his eyes but amusement at the situation. Dean’s stomach fluttered like crazy and he wanted to just lean over and kiss that beautiful smile right off of Cas’s face.

Castiel’s blue gaze meets Dean and he smiled kindly as if giving Dean a peace offering. Charlie watched the two with a smile on her face. She knew that bringing Castiel here tonight was a risky choice that could have potentially torn apart her friendship with Dean but it also could finally give the teen the boost he was probably never going to get otherwise.

Dean clears his throat awkwardly, “Uh, I am really sorry about what happened that day. I hope your customer wasn’t too upset.”

With a coy smile, the other boy just shrugged, “Balthazar is a regular and he actually found the interaction quite amusing. I have yet to hear the end of how I leave boys a stuttering mess.” Castiel said running a hand through the mess of hair on his head.

Charlie chuckled next to Dean and was probably about to make some witty remark when their waitress decided to finally make her grand entrance. Dammit where was she five minutes when Dean needed her.

She was honestly a very pretty thing that normally Dean probably would have flirted with if Castiel wasn’t sitting across from him, eyes still boring into Dean’s head.

The waitress, Candice as her name tag read, asked for the drinks not even seeming to notice the air of awkwardness that was currently surrounding the table. Instead her attention seemed to be focused solely on getting Cas's attention which irked Dean to no end as he watched her lean across the table to pick up the menus and shove her boobs in his face. Was that seriously necessary? Even Charlie was a little perturbed by it and she was into chicks. However Cas wasn't even fazed by the waitress and he kept his eyes on Dean and only Dean making the teen blush slightly.

They ended up ordering their food as well just wanting the girl to leave them alone for as long as possible. Both guys ordered cheeseburgers making them grin at each other. "Man the burgers here are awesome" Dean told Cas finally starting to relax a little once he realized that Castiel wasn't just here to make fun of him and might be genuinely interested in Dean.

The other teen just grinned, "I guess we’ll have to find out. I must warn you I've had some pretty good burgers in my life Dean. They are, after all, my favorite food."

The other boy just smiled and blushed a little, rubbing the back of his neck, “Well I have to admit I can make a pretty mean burger myself, although I would have to say pie is definitely my favorite food, burgers being a close second.”

Charlie chuckled next to them shaking her head, “Men and their food. Next think I know you guys are going to be discussing cars and sport teams.”

Dean snorted and rolled his eyes, shoving Charlie playfully, “Hey even you have to admit that baby is beautiful” he said thinking about his beautiful car in the parking lot; and so what if Dean had a love for cars, he also had a love for women’s underwear so he was pretty sure he didn’t fall under the normal male stereotype.

She just rolled her eyes, “of course Dean,” Charlie huffed out and then leaned across the table towards Cas, “Baby is what he calls his car which he is overly attached to, I’m pretty sure he would make love to her if her could”

“Charlie!” exclaimed Dean as he shoved her again, making her laugh as she hit the window. “Stop being dramatic,” he was scared Castiel was going to get the completely wrong idea of him, not that his current image was probably that great.

But Castiel just smiled, “I would love to see her at some point. I don’t have a car or a license actually since I am too scared to have my brother teach me but I have always liked cars. I wished I knew more about them.”

Warmth spreads throughout Dean’s chest as he thinks that this right here is where he has some common ground, where he can redeem himself with Cas and really have an excuse to talk to him, “Well I can teach you? I actually work at a garage,” Dean offered with a shy blush creeping up his neck which he tried to ignore.

Castiel’s eyes light up and he beamed at Dean, “Really!? Dean I would love that! What type of car do you have?” he asked leaning a little closer even though there was a table in the way.

Charlie rolled her eyes and mumbled under her breath, “See I knew you guys were going to talk about cars.” She ended up pulling her phone out and playing with it leaving the two boys to talk.

The grin on Dean’s face could not be matched at this point, “I have a 67’ Chevy Impala. I actually had to rebuild her from the ground up myself last year.” He was about to say more but the waitress once again made her presence known by setting down their drinks in front of them and then their food. His stomach growled loudly again as the steaming burger was placed in front of him. God it smelt so good too. Dean grinned over at Castiel who had a look of bliss on his face when his own burger was set down in front of him.

The waitress grinned and leaned against the table, “Can I get you anything else?” She asked looking only at Castiel who finally seemed to notice the attention she was offering him. His face screwed up in a look that made it obvious he was uncomfortable so Dean reacted on instinct reaching across the table and taking Castiel’s hand, threading his fingers through the other boys.

“No we’re good but thanks,” he said with a smirk as the waitress eyes went wide and she blushed.

“Oh…” she swallowed and couldn’t tell if she wanted to be disgusted or just run away. “Enjoy your meal” she squeaked out before hurrying away.

Dean sat back laughing as she ran off, looking over at Castiel who was staring at him with amusement, eyes crinkled up and shining bright as he watched Dean, their fingers still intertwined.

“Thank you for that, she was making me very uncomfortable. I am not used to such attention.” Castiel said glancing down at their hands.

Dean tensed up when he realized that he was in fact still holding Cas’s hand. It just felt so right, his palm was warm and smooth. How could someone’s hand be so soft? His fingers were long and graceful, giving the green eyed teen a wonderful fantasy of pulling those digits into his mouth and sucking on each while keeping eye contact with him. Dean shuddered and quickly removed his hand from the others, his face burning hot as he desperately tried to think of something sad to stem the flow of blood that was quickly heading south. 

Castiel raised an eyebrow at him but didn’t say anything instead just picking up his burger and taking a bite. He let out a low moan as the food was chewed up and swallowed, leaving Dean still struggling with a hard on. Cas just continued to eat pretending to be completely oblivious to the other teen’s on the other side of the table from him.

Dean lets out a little whimper and dove into his own food as an attempt to distract himself from the god in front of him. Charlie was almost done with her own food as she had sat there and observed them the whole time, internally patting herself on the back for a job well done. She pushed her plate away, when the other two were only half way through their food, no one had said a word at this point.

“So I actually have to be getting home, but like said my treat so here’s my card. You two have fun!” she said squeezing out of the seat behind Dean who tried to pin her but Charlie was a sneaky son of a bitch. “Hey Dean you wouldn’t mind giving Cas here a ride home right?” She paused not long enough for him to actually answer, “No I didn’t think so. Alright you kids have fun, be safe, don’t do anything I wouldn’t.” She winked and then scurried off before either of the boys had swallowed their current bite of food.

Dean growled and shook his head, “I’m going to kill her one of these days” he said sliding her card towards him and trying not to panic at the thought of driving Cas home, “Hey at least you’ll get to see my car”

Castiel finished up another bite of food before answering, “Very true, I am quite excited about that. But you don’t have to take me home. I can always walk or take the bus”

“Uh hell no man, I am assuming you live about the coffee shop and that’s on the other side of town. I’ll drive you, it’s no problem, really” Dean said smiling even though his heart was about to beat out of his chest.

A grateful smile light up Cas’s face, “Thank you Dean, that is very kind of you. Now shall we order some pie?” he said with a smirk.

“Hell yeah” was Dean’s response as he quickly finished his food and then waited for the waitress to return. She did and this time she left as quickly as she came with their orders for two slices of cherry pie.

“So are we going to talk about your stalking habits?” Castiel asked sending Dean a coy smile. He loved making the other boy squirm and blush.

“What..” Dean stuttered out once again blushing, “I’m sorry… I just happen to like that store a lot. It’s honestly just a coincidence. And I really didn’t know that your brother owned that coffee shop, I just didn’t want to go to Starbucks.”

Castiel laughed as Dean spluttered and choked trying to explain himself, “Dean I really don’t mind. I think I enjoy looking at you as much as you enjoy looking at me”

Well shit, what the hell was he supposed to even say to that? Luckily this time he was saved by the waitress as she delivered the pie and their check. Dean quickly dug into it the pie, groaning at how good it tasted and trying to ignore the other man whose was just sitting there with a smirk. They didn’t say anything as they finished up the pie and paid the bill.

Dean stood up awkwardly from the booth not knowing what the hell he was even supposed to say. Castiel stood up next to him eyeing Dean almost as if he was a scared animal. The walk out to the car is tense to say the least but when they get to the car Castiel grinned, “Dean you’re car really is beautiful!” he exclaimed running a hand down the hood and marveling at it.

It helped break a lot of the tension, and the other teen smirked while crossing his arms and leaning against the hood. “I know.”

Castiel looked up at the smugness in Dean’s voice and walked over to him with a playful look in his eyes, “Almost as beautiful as the imagine of you in those panties was” he said quietly planting his feet in front of Dean’s his eyes teasing.

All the blood rushed to the green eyed teen’s face at those words and he fidgeted nervously not believing that Cas was actually fantasizing about him! His heart was pounding a mile a minute as he tried to figure out whether Castiel was actually interested in him or was just doing it to mess with him. Dean’s pretty sure his heart would break if it turned out to be the second.

“Cas…” He whispered out hoarsely, “What is this? Are you actually interested in me or are you just fucking with me?” Dean choked out remembering the boys comment at the store yesterday.

Castiel’s face fell and he took a step back, “Dean… my apologies. I did not mean to make you so uncomfortable. I thought I was making my interest in you quite obvious, I didn’t even think you might take it any other way.” He stepped back up to Dean and cupped his cheek. “Yes Dean, I am very interested in. Since the day you walked into the store to the moment you knocked coffee all over Balthazar. All I have wanted was for you to get the courage to talk to me.” He rubbed his thumb gently along Dean’s cheek before letting his hand drop away eyes pleading with the other to understand he never meant to lead him on or to hurt him.

Dean’s breathing was ragged and his heart was in his throat. He couldn't help but lean into the touch wanting more of it. It left Dean’s skin tingling and him with the urge to turn his head and kiss the palm of Cas’s hand. It just wasn’t real; it couldn’t be real that this man, this beautiful, amazing man actually wanted him. If he had known Cas wanted him this badly Dean would have approached him years ago and saved them both the trouble. “Fuck Cas… I…” He was completely at a loss for words. So instead, Dean reached forward and grabbed Castiel by the lapels of his coat and pulling him flush against his body, an ankle hooked around his, and kissed him square in the mouth like he’s been dying to do since the moment he saw Cas. 

The other man gave a little squeak in surprise, his hands catching himself against the impala before coming to wrap around Dean’s neck as he melted into the kiss. It was perfect in every way, slow, sweet, and moving. Dean tasted like cinnamon sugar and pie; it was better than anything the teen had previously imagined.

Dean slid his hands down to Cas’s waist to steady him as their kiss deepened. He was pretty sure no first kiss was ever going to beat this. Castiel tasted amazing, it was almost impossible to describe, like honey but sweeter and there was almost an electric like charge to it. Dean was pretty sure he would kiss Cas forever if it was possible.

However it wasn’t possible as both boys needed to breath. They pulled apart panting, lips swollen and eyes blown wide. Neither one of them said anything while they gained back their breathe, instead just leaned against each other taking the other in.

Finally Dean spoke up as he ran a lazy hand through the back of Cas’s hair, “We should probably get you home. I don’t need Gabriel coming after me” he said with a chuckle his other hand rubbing circles into Cas’s lower back.

The blue eyed teen groaned and laid his head on Dean’s chest, “Yes you are probably right although I do believe Gabriel will be more than happy about this turn of events.” He pulled away and straightened his coat out.

Dean chuckled and leaned over to give him another peck before moving to get into the driver’s side of the car, having to shift a little at the uncomfortable bulge starting to form in his pants.

Both boys couldn’t help the shit eating grins that were plastered on their faces as Dean started the car and drove away. They were both silent, just thinking about what had just transpired. When Dean pulled up in front of the coffee shop he turned the car off and looked over at Cas who was still slightly flushed.

“Thank you for the wonderful evening Dean,” Castiel said this time being the one to blush. “I have already put my number in your phone if that is acceptable?”

Dean looked at him surprised until he realized he had left his phone sitting on the passenger seat, “That is very acceptable,” he said with a smirk leaning over to kiss Cas one last time. This kiss didn’t last as long but it was just as passionate and both boys were red in the face when they pulled apart.

Castiel climbed out and waved to Dean before going into the shop leaving Dean to sit out there and just think about how fucking soft Cas’s lips were.

He grabbed his phone and found Castiel’s number right away,

To Castiel: We are definitely doing that again ;D

Dean drove away with a smile on his face.


	6. Chapter 6

**Summary for the Chapter:**

> Sam doesn't care, and Dean is relieved.

**Notes for the Chapter:**

> Hey there... so wow, yeah I know it's been a long time since I've updated and anyone who is still reading this thank you so so so much for your continued support. I've been suffering from some major writers block as well as just no time to sit down and try to write. 
> 
> If anyone has a certain direction they would like to see the story go please leave a comment below! If not it will be ending here in a couple chapters. :) 
> 
> Follow me on tumblr, Casorpiedeanwinchester 
> 
> Also for any of you who love to write you should follow destielficletchallenge! We will be hosting another challenge soon (Holiday themed!)

Dean couldn't stop thinking about Castiel for the rest of the night and all through school the next day. Even Sam noticed the change in his brother causing him to raise an eyebrow but he didn't question it, it was nice seeing Dean happy for once. The two teens had been texting none stop since Dean got home from dropping Cas off. So far Dean had learned that Castiel's favorite color is green and yellow, he has a strange obsession with bees, loves classical music, and everything that has to do with history. Apparently the dude was a real nerd, top of his class, and already in line for scholarships. That made Dean's chest a little tight, they weren't even officially dating yet or anything and already he felt a strange attachment to Castiel. Just the thought of him going off to some big fancy college and leaving Dean behind left a hollow ache in Dean's chest. 

It wasn't till almost one in the morning that they both decided it was probably time to go to sleep and they would talk again later. Dean set his phone aside and stared up at his ceiling a goofy smile still plastered on his face. "Geeze when did I become such a sap," he thought running a hand over his face. He rolled over on to his side and curled up with his hands tucked under his pillow as he once again thought about those soft, chapped lips and blue mesmerizing eyes. Dean sighed and smiled rubbing his face into his pillow still not believing that someone as smart and beautiful as Castiel would have any interest in him. It's not too long after that, that Dean eventually slips off to sleep, his dreams filled with all things Cas. 

The next morning Dean woke bright and early which was unusual for him especially considering the late hour he fell asleep. He slipped out of bed and walked to the kitchen yawning and running a hand through the mess on his head known as his hair. Before he can even get started making coffee his phone is already going off with texts from Cas. 

**From Castiel: You know for living above a coffee shop I have a strange dislike for all things coffee related.I much prefer the soothing effects of a good cup of tea.**

**From Castiel: My apologies if I woke you up, I like having time to observe my bees before going to school.**

**From Castiel: Did you know that all honey worker bees are females?**

**From Castiel: Also honey bees can recognize faces.**

Dean grinned down at all the texts, Cas was such nerd. He did this last night too, sprouting off cute random facts to Dean about things Dean had honestly never heard of. He also texted with perfect grammar, Dean wondered if Castiel even knew what 'lol' meant. 

**_To Castiel: Don't wrry u didn't wake me. So u actually have bees in your backyard!?!?_ **

Dean shook his head and pulled out a couple pans to start making breakfast. It was rare for him to cook on school mornings but this morning definitely wasn't going as normal. Sam walked out of his room, hair sticking up everywhere and a surprised look on his face. A big yawn that Dean swore made Sam's jaw hit the ground greeted him before Sam was moving around him to get the milk from the fridge. 

"I want to ask why you're up this early but at the same time I would rather not ruin your unusually, disgustingly happy mood. I don't think you've stopped smiling since last night. Care to share with the class here what happened?" Sam asked as he leaned against the counter and poured himself a tall glass. 

Heat rose into Dean's cheeks as he cracked eggs open over the pan. Had he really been smiling that much? "Uh nothing really. I just had some fun with Charlie and our friend Castiel last night. You would like him, he's a real nerd like you." 

Sam scoffed and took a sip if his milk, "I'm not a nerd" he mumbled before sighing and moving to sit at the table and wait for the food, "But I am happy you're happy." Sam said grinning at his brother. 

Dean rolled his eyes and piled eggs and bacon on to two plates, "Yeah whatever you say bitch," said Dean as he set the food down in front of Sam. 

"Sorry for caring Jerk!" he shot back before digging into the food, "Damn Dean you did good this morning." 

Dean snorted, "What are you trying to say? That my food normally sucks?" he said before taking a bite of his food, his eyes moving over to glance at his phone waiting for Castiel to text him back again. 

Sam groaned, "Yeah Dean that's exactly what I'm saying" he replied sarcastically. 

Dean ignored Sam's comment because his phone decided to go off right then. He jumped up so fast he almost knocked over his cup of coffee. Sam grabbed the table to keep it from shaking as Dean raced over to his phone and pulled the text up with a happy grin. 

**From Castiel: Yes, I have bee's in my backyard. Gabriel doesn't like it but he seems to find himself having a hard time saying no to me. I also do not do much other then work and go to school. I think, he thinks it gives me something else to do.**

Dean smiled and then shook his head, it was ridiculous that he was this happy about a stupid little message over a phone. He glanced over at his brother and Sam was watching him with wide, questioning eyes. A hot blush rose on Dean's cheek and he turned his back to his brother feeling embarrassed. How was he supposed to explain to his brother that he was completely and totally head over heels for a guy. What if he found it disgusting and doesn't look at Dean the same way. He swallowed nervously and the happiness he felt a moment ago from Castiel's text slowly drained out of him as quickly as it came. 

Dean sat his phone down on the counter and moved back over to get his food suddenly not feeling hungry at all. Sam noticed the change right away and was about to say something but the look on Dean's face made him think better of it. He wondered what that text had said, Dean seemed so happy to be getting it. Maybe that was the person who was making his brother so happy this morning and last night. Which made Sam wondered just what that text could have said. 

The remaining food on Dean's plate found its way to the trash can before the older teen dropped it into the sink with a loud clank and then sulked his way down the hallway to his room. The rest of the morning he could barely find the energy to put his clothes on. It hurt so much thinking that he needed to decide between his brother or having Castiel. He couldn't ruin his relationship with his brother, it meant more to him then anything in the world. 

A knock on his door made Dean jump and he spun around clutching his shirt to his chest. "Sam?" he called out knowing that it couldn't be anyone else. 

Sam pushed the door open holding his phone up, "It kept going off. Castiel sounds like a really nice guy Dean." He said placing the phone on the bed and watching his brother. As soon as the phone had started going off again, Sam had picked it up not meaning to read his text's but it was hard when they were lighting up the screen. That's when he saw a text from this Castiel person saying that they still couldn't believe last night had happened. That's when it dawned on him, his brother was gay and was scared. He swallowed; did Dean really think that he would care? It made Sam feel sick to his stomach that his brother felt he couldn't trust him with this. 

Dean watched with wide eyes as Sam dropped the phone on the bed. "I... I can explain..." Dean started feeling like everything was about to collapse around him. 

Sam just held his hand up and walked over to his brother pulling him in for a tight hug, "Dean, I don't care if you're gay, I don't care who you love. All I care about is that you're happy." Sam whispered hoarsely into Dean's ear, squeezing his brother. 

Dean's chest felt too tight and he couldn't breath. He was sure Sam was going to tell him he is disgusting and unnatural. The last thing Dean expected was to find himself wrapped in the warm embrace of his brother being told that it was okay, it was okay and he didn't care. His throat was too tight and Dean almost made a choking noise as he clung to his brother. "Thank you" he whispered back already feeling the tension from earlier slowly draining out of his body as realization dawned on him. Sam didn't care, it didn't matter to him that Dean was currently, maybe falling in love with a guy. 

Sam pulled back with a grin and then slapped Dean on the shoulder glaring at him, "Don't make me beat you next time. You can tell me anything Dean" he said earnestly. 

With a grin and a playful shove at Sam's face, Dean just smirked, "whatever you say bitch." 

"Yeah, alright jerk!" Sam said pushing away from Dean and heading back out of the room, "Come on old man we're going to be late for school." 

Dean chuckled and finished getting ready, slipping his shirt on and picking up his phone to read Castiel's texts. 

**From Castiel: I really don't want to go to school today for the first time ever.**

**From Castiel: I would prefer sitting here and talking to you.**

**From Castiel: I still cannot believe last night really happened.**

**From Castiel: You have nice lips ;)**

Dean couldn't help but laugh out loud at the last comment. Even from the short time he's known Castiel that seemed so out of character for him. He jumped when his phone went off again and Dean opened the next message. 

**From Castiel: My sincere apologies Dean, my brother stole my phone. I did enjoy last night however.**

Dean shook his head and grinned again, he typed out a quick reply,

**_To Castiel: It's cool Cas. What do u say Friday night I take out? There's a fair in town maybe we could go?_ **

The reply took longer than Dean was expecting and it made him nervous. Finally the phone dings and Dean opened the message so fast he dropped his phone. 

**From Castiel: I have never been to a fair before. What does one do at a fair? Regardless, my answer is yes. I would love to go out with you Friday night Dean.**  

If anyone could see Dean right now they could quite possibly say that he was almost literally glowing with happiness. 

_**To Castiel: Have u really never been to a fair? Well I guess youll see when we get there ;P** _

Dean smiled and slipped his phone into his pocket as Sam shouted out that he needed to move his ass. Oh yeah, this week was going to be awesome. 

**Notes for the Chapter:**

> This chapter was shorter then I was planning because originally I was planning on having the date in this chapter but then everything with Sam happened. So this is what you got instead!! Next chapter should be longer and it will include the date :)
> 
> This is un-betad. Please leave a comment below.


	7. Chapter 7

**Summary for the Chapter:**

> Dean deals with some bullies. 
> 
> Castiel rides a Ferris wheel.

**Notes for the Chapter:**

> OH MY GOSH LOOK AN UPDATE!!!!!! 
> 
> Holy crap I am so sorry to all of y'all for this taking close to a year for me to post!! It's been my senior year of high school so I was just focusing on trying to get out alive! 
> 
> But here you go! A pretty long chapter for you amazing people!!!!! There will only be two more chapters after this, one will be all smut ;) and the other will be the epilogue. 
> 
> Thank you so much to those of you guys who are still reading this! Also going back through the older chapters I realized just how many grammar errors there were and I will be going back and fixing those; perhaps even adding in some more detail. 
> 
> Follow me on tumblr at casorpiedeanwinchester

Dean woke up Friday morning not believing that it was finally the day of Cas and his date. It had felt like every day that week had dragged on ridiculously longer than necessary. Dean laid on his back and starred up at his ceiling with a smile on his face. Today was going to be awesome.

The teen climbed out of bed once he heard his brother shuffling around, not even finding it in himself to be reluctant about going to school today. After all the faster school was over today the faster he would get to see those gorgeous blue eyes again.

One quick bowl of cereal and an apple later, Dean was in the car almost shaking with anticipation for the coming events. He even beat Sam to the car he was so ready for the day to get started and for it to be 5:30 already. Sam just shook his head and took his sweet ass time getting to the car knowing that it would irk his brother. Dean even threatened to leave him behind but they both knew he wouldn't actually do it.

Dean finally arrived at school, on time for once too, and was greeted by a grinning Charlie leaning against a tree by Dean's usual parking spot.

"So how is our little love sick puppy doing?" The red head teased, "all ready for tonight?"

Dean rolled his eyes and makes sure the Impala was all locked up before he fell into step next to her. "You know you're just jealous that I have a hot date tonight and you don't."

Charlie huffed and pouted, "and who says I don't have a hot date tonight?"

Dean smirked, "Because I wouldn't have been able to have gotten out of my car without you already attacking me with 'cute' text messages between you two and about how smoking hot she is. Come on Char, I know you."

The girl stuck her tongue out at Dean and stomped off towards their lockers, her red pony tail swinging dramatically behind her. Dean grinned and followed knowing she wasn't really mad at him.

"You're lucky I like you Winchester," She hissed when Dean caught up to her but of course there was also a huge smile on her face.

He smirked and shrugged, "Uh who couldn't like this face! Do you not see how adorable I am!" Charlie shoved him then and Dean fell back against the lockers laughing while trying to avoid Charlie smacking his arm again.

"Hey Winchester!" A sudden voice shouted from down the hall pulling the two teens away from their fun. Spinning around, they find none other than Alistair and his crew sauntering towards them. "Heard that some of the boys saw you sucking face in the parking lot last night, accept what surprised us all was the lack of boobs on said person you were kissing." Alistair said looking around at the people standing next to him who were nodding their heads and trying to look cool but really they were all nervous little shits.

Dean grinded his teeth together and slowly turned and stepped in front of Charlie to make sure she wasn't going to get hurt if anything happened to break out between them. "Oh is that so?" Dean said, "Doesn't seem like a problem to me? I mean really who I choose to kiss really shouldn't be concern to any of you. Unless that is one of you is jealous."

Alistair growled and Gordon spoke up, "We don't need to be having any faggots on the team! Now we all have to worry about whether you're going to try and fuck us if we bend over the wrong way."

Dean gritted his teeth together and tried his hardest not to punch the bastard in the face, "trust me the last thing I would ever want to do would be to ever touch the likes of any of you. Pretty sure I would end up getting some sort of STD from how many people you have screwed around with, or well... at least attempted to."

Gordon took a step towards Dean his fist clenched in anger but Alistair held him back, "Resign as captain of the baseball team and tell coach you think I should be captain and we'll leave you alone." Alistair growled out through clenched teeth, hopping to form some sort of compromise.

"No!" Dean retorted angrily, "I'm captain fair and square and I'm sure as hell a better player and captain than any of you guys ever will be. Why don't you grow up and realize that you don't own this earth let alone this school."

The boys standing behind Alistair looked at each other skeptically like they agreed with Dean but were just too afraid to say anything.

"Alistair you're just a giant bully, and you're just mad because we all know that you have a giant crush on Dean!" Charlie suddenly spoke up from over Dean's shoulder holding up her phone, "I even have the proof right here. So unless you want me to show the entire school what you fantasies at night about, you better put your tail between your legs and run off like a good dog."

Alistair's face suddenly went red with embarrassment and everyone looked at him in surprise while Charlie just stood there, a triumphant look on her face. Dean shot her a grateful smile although he's seriously curious about these so called fantasies.

Alistair clenched his fist and stepped towards Charlie about to punch that no good, noisy red head in the face. But Dean will have none of that and Alistair finds himself on the floor with a bloody nose before he could take another step.

Dean glared down at him, standing protectively in front of Charlie who was peeking out from under his arm, "You ever think about hurting someone I love Alistair and it will be the end of you." Dean spit out in anger, "And the rest of you, why don't you grow a pair and learn to think for yourself instead of following this pathetic waste of space around." Dean stepped over Alistair followed by Charlie who may or may not have accidently kick the body on the ground. The other boys backed away quickly, a nervous look on their face as they watched their leader groan in pain on the ground.

"Good day boys!" sang Charlie as she followed Dean towards class.

\-------------------------------

Dean sat in first period fuming. He was now even more motivated to come out then he had ever been before. Who do those dick heads think they were to try and dictate what he can and cannot do in his life. So much for his good mood. Dean gripped his pencil hard trying to pay attention to his teacher but was unsuccessful. However his phone chose then to buzz inside his pocket and Dean pulled it out to see a text from none other than Castiel.

**From Castiel: Good morning Dean! I am very excited for this evening. It also seems that Gabriel spiked my tea this morning with something and I'm very hyper because of it.**

Dean was barely able to hold back a chuckle and almost instantly his bad mood was broken. How could he stay mad when someone this adorable was texting him?

**_To Castiel: I'm very excited for tonight as well, I will pick u up from the coffee shop at 5:30. Uh, maybe u should keep a better eye on ur tea next time? Hahaha!_ **

Dean slid his phone back into his pocket feeling ten times better and that maybe today woyldn't be impossible to get through after all.

**From Castiel: You're probably right... I shouldn't trust him when he offers to make me breakfast and tea because I deserve a day to sleep in.... I shouldn't trust him period. This is Gabriel we are talking about after all.**

**From Castiel: Dean my hand is tingling!!! Is this normal!!!**

**From Castiel: I think I should go to the nurse!**

**From Castiel: I'm going to kill Gabriel.**

Dean couldn't stop grinning. Oh yeah today was going to be awesome.

* * *

The rest of the day went by without further incident. Neither Charlie nor Dean saw anything of Alistair or his crew for the rest of the day making it an unusually peaceful day. Dean hurried home right after school thanking god that Sam had offered to go over to a friend's house after school.

A quick shower and some cologne later, Dean was nervously shrugging on his jacket thanks to a random cool front that decided to blow in and getting into his car. He was dressed simply in a pair of jean and a green button down that he had been told really make his eyes pop. His leather jacket was warm and comfortable against the chilly breeze that was blowing up and making everything a whirling mess.

Dean pulled up in front of the coffee shop at 5:20 feeling like he might throw up. Should he get out now or wait till 5:30? Will he seem to eager? Or too late? Dean started to hyperventilate as he over thought about what he should do. " _This was a guy, not just some random chick, what if the rules are all different, what if I screw up somehow and Castiel gets mad at me?"_ Dean thought as he sat there gripping the steering wheel. Suddenly his passenger door opened and a warm body slid up against him quickly ending Dean's current train of thought.

"Hello Dean," a wonderfully familiar voice whispered into his ear making a shiver run down Dean's spine that wasn't due to the cool breeze that snuck in with the open door.

Turning his head, Dean focused on Castiel not even a hairs breath away and couldn't help but lean in and claim those slightly chapped lips in a soft, welcoming kiss. Dean pulled back with a hum, "mm hey there Cas."

Both boys were grinning at each other as Dean started the car. They headed out with their fingers twined together on the seat between them.

"So I'm assuming you're feeling better from your earlier ordeal?" Dean asked Castiel eyeing the boy from the side of his eye, a small chuckle escaping from his throat.

Castiel huffed, an annoyed looking crossing his face, "Yes I survived, luckily. Gabriel is an assbutt and I had to lay in the nurse for an hour drinking tons of water to try and wash the stuff out of my system. It was not fun, I peed so much." said Cas, glaring at the window like he wanted to break it, possibly picturing it as Gabriel's face.

Dean squeezed his boyfriend's hand pulling his attention back to the present moment, "Hey don't worry about it. Tonight is going to be awesome! We're going to eat fatty food, win some prizes and just have an awesome time okay? No worrying about anything" He smiled, looking over at Cas for a brief moment before pulling his eyes back to the road.

Castiel grinned and laid his head on Dean's shoulder. "You're incredible," He whispered out.

Dean swallowed thickly not knowing exactly how to reply so he just turned the radio on to fill the silence until they arrived at the fair.

When they pulled in not more than fifteen minutes later, the fair grounds were already packed with children and families. The streets were lined with cars, and one could smell the fried food cooking from a mile away. There was music blaring through speakers, filling the air with vibrations while children's screams and laughs followed the chorus.

Dean grinned as he found a safe place to park his baby, already feeling excitement bubble up inside. Fairs always did that to him and he hoped Castiel was feeling the same excitement as he was. Judging by the twinkle in those blue eyes and the grin plastered on his face, Castiel was definitely ready to hit the grounds.

Once out of the car, Dean took Castiel's hand in his, trying not to let himself over think this again. They headed to the ticket booth were Dean paid for both of them, ignoring Castiel's protests. Dean also bought them each a round of tickets to use at the game booths.

"You ready for this?" Dean asked with a grin as he led Cas through the lit up gate.

Castiel was bouncing on his toes with anticipation as they entered the fair grounds. Once inside, the black haired teen let go of Dean's hand and spun around in a circle trying to take it all in. There were booths with different kinds of food, ring toss games, water games, picture booths, a huge Ferris wheel that Castiel had to lean his head back to see the top of, and many other rides and games. Everything was lit up with flashing lights and big signs making the whole place glow brightly even in the dimming light of the evening.

"Dean this is amazing!" Castiel shouted out. He grabbed Dean's hand and pulled him over to the first booth game. "Okay so how do you play?" Cas demanded to know looking at Dean with big blue eyes.

The other teen hadn't been able to stop smiling as he watched Castiel take it all. Dean thought he looked just like a little kid, awed by everything around him. He couldn't help but chuckle as Castiel dragged him over to the closest game and demanded to know how it worked.

Dean paid the guy two tickets to play and then lifted the darts up. "Simple, you have to try and pop the balloons. If you pop all three you get a big prize, and if you only pop one you'll get a small prize." Dean explained waving at the toys around them.

Castiel nodded his head and took a dart from Dean. He bit his lip in concentration as he eyed the balloons in front of him. He threw it and missed making a frown appear on those chapped lips.

Dean leaned forward and kissed his cheek, "It's okay babe, you can try again it was only your first time. Trust me it's harder than it looks."

The guy running the booth eyed the little show of affection but kept whatever comments he had to himself.

Castiel managed to pop two balloons with his last two darts much to Dean's surprise. The teenager jumped with glee and clapped his hands a little before realizing how silly he must have looked and tried to calm down. Dean just laughed though and took the small stuffed animal the man handed to him as Castiel's prize.

"Can we play again!" Castiel asked wanting to win the big prize.

Dean just shook his head though, "Come on, there's lots of games to play but only so many tickets." he said wrapping an arm around Castiel's waist and leading him away from the dart game.

Castiel pouted for a moment, making Dean want to just pull him into a secluded corner and make out. The green eyed teen controlled himself though and they headed over to the next booth.

This one was the ring toss one, which involved getting little rings around the tops of bottles. The bottle in the middle was green and you won the big prize for getting it. Neither Castiel nor Dean ended up being any good at it though and Castiel even ended up hitting the person working the booth with one of this rings.

Dean couldn't stop laughing at the faces Castiel made when he threw his rings and almost ended up falling over when Cas hit the worker. The boys left after that, standing closer to each other than before, hands swinging between them.

The stopped at a booth to get food next. Dean ordered a turkey leg while Cas got the roasted corn. They ended up sharing their food though, each taking bites of the others. The continued walking, getting closer to the Ferris wheel. Castiel looked up at it and grinned.

"Dean! Can we ride the Ferris wheel? I've never been on one before?" Castiel asked with big blue eyes full of longing.

Dean felt his stomach drop as he too looked up at the daunting wheel of death in front of him. His legs shook as he looked at just how high it went. Every possible scenario of what could go wrong flashed briefly through his head. But he couldn't disappoint Cas.

"Sure!" He said his voice sounding a little more high pitched than normal. Dean cleared his throat wishing now that he didn't have food in his stomach.

Castiel didn't seem to notice however as he pulled Dean to the back of the line bouncing with excitement.

They reached the front of the line all too soon for Dean's liking and he handed the girl running the ride their tickets.

"Enjoy" she said in a monotone voice as she locked them into silver death trap.

Castiel gripped Dean's hand as the ride began to turn. He looked out onto the grounds watching as they got smaller and smaller. "Dean this view is amazing!" Castiel shouted looking over at the other man to find him pale and his eyes closed. "Dean?"

"Uh... uh yeah awesome view." he said not opening his eyes. Of course the ride decided to stop then right at the top. "Shit," Dean squeaked out as he felt the cart rock back and forth.

Castiel's eyes went wide with understanding. "You're afraid of heights?" He asked scooting closer to Dean.

"Uh... okay maybe just a little," Dean choked out trying to focus on anything but the rickety cart they were trapped in.

"Why didn't you tell me! Dean we didn't have to go on this." Castiel said softly trying to get Dean to focus on him.

Dean looked into the other mans eyes and felt himself calm down marginally. "I wanted you to have the full experience." He whispered out.

Castiel smiled and wrapped a hand around the back of Dean's neck. He pulled him in and kissed Dean deeply making the other teenager completely forget his surroundings for the moment. Castiel wrapped a hand into Dean's hair and tugged lightly causing the other boy to gasp in surprise.

The ride started to move again but Dean didn't even notice this time as Castiel kept distracting him with delicious kisses. By the time it was their turn to get off, both their lips were swollen and Dean's hair was a complete disaster.

The girl at the bottomed smirked at them but said nothing as the two climbed out hand in hand.

The rest of the evening was a hit. They played some more games, with Castiel being really good at the basket ball one much to Dean's surprise. They ended up having so many stuffed animals that Dean had to carry them back to the car before they could continue on.

As the night wore on, a live band started to play and Castiel pulled Dean out on to the dance floor. At first the music was fast and pop like, which made Dean feel awkward as he stood in what was basically a mass of sweaty bodies and just grinded on each other.

Then a slow song came on and the next thing Dean knew Castiel was sweeping him away, twirling them around in circles with an arm around Dean's waist. He blushed a little, yet couldn't help but pull Castiel closer and rest his head against the others.

Dean quickly found himself lost in those azure blue eyes and everything around them seemed to just disappear. The noise of kids yelling faded away along with the bright lights, leaving nothing behind but Castiel. Everything was Castiel.

Both men stopped moving and just stood there starring at one another. They didn't notice the song change until people were bumping into them as they moved to the faster beat.

Dean shook his head and cleared his throat, "Uh, you want to get out of here?" he asked softly.

Castiel grinned, "Definitely."

Dean felt his stomach jump but he wasn't sure if it was excitement or nerves for what could happen next. The two boys hurried out to Dean's car, where Castiel pinned Dean up against the door and kissed him deeply. When he pulled back, Dean was having to gasp for air. Every kiss with Cas took him by surprise it seemed.

"Get in the car now," Dean growled out feeling arousal pool deep in his stomach.

Castiel grinned with excitement and quickly slide into his seat.

"My house, Sam's at a friend's." Dean grunted out as he started the car and took off way too fast down the road.

Castiel smirked and slid over to Dean. "Someone's eager." He whispered into the others ear before taking it in his mouth and tugging lightly at it.

"Shit!" Dean cursed trying to keep his focus on the road in front of him.

"Excuse you, is that the type of language you should be using young man?" Castiel said as he slide a hand over Dean's thigh and squeezed it.

"Dammit Cas!" Dean practically shouted.

Castiel chuckled almost evilly and slid back over to his side of the car. Dean breathed a sigh of relief but at the same time he missed Cas's warmth.

They pulled into Dean's driveway with a squeal of tires and Dean cut the engine. He looked over at Castiel to find the other man smirking at him.

"So, do I finally get to see you in those panties?" He asked with a wink before climbing out of the car and sauntering towards the front door.

_Oh my god._ was all Dean can think as he scrambled after the other boy.


	8. Chapter 8

**Summary for the Chapter:**

> Sex. That is it. Just Sex.

**Notes for the Chapter:**

> So this is the last chapter! And I will upload an epilogue, or many just one more chapter. I don't really know if it will be an actual epilogue or not. But I can't believe I am actually about to finish my first fic to the end! Even if it took a lifetime. 
> 
> This chapter is basically all sex, tell me what you think!

Dean fumbled with his keys as he hurried to open the door. Castiel was leaning up against him, kissing the back of his neck as his hands wandered up the front of Dean’s shirt. Dean let out a surprised gasp when Castiel twisted his right nipple. “Cassss” Dean whined as he finally managed to get the door to fly open. They stumbled through ungracefully but neither boy cared as they tugged at the others shirt. Castiel kicked the door shut behind them with one foot as he shoved Dean against the wall, pinning the green eyed boy with his hips. Dean groaned, his cock straining against the zipper of his jeans. 

Castiel leaned in close enough that his lips were just grazing the soft skin of Dean’s ear, “I’m going to give you two minutes to get to your room and put on those red panties I liked so much.” Dean felt a shiver go up his spin and he thought he was going to come right there and then. He swallowed thickly and somehow managed to nod his head in response to the beautiful man shoved up against him.

Castiel smirked and stepped back, “Good boy” he said silkily. 

Dean groaned and stumbled away from the wall towards his room. He felt like a horny teenager going through puberty all over again. He tripped over his pants in his attempt to get to the box hiding his most precious items. 

“One minute left Dean!” Castiel called out, and Dean cussed as he heard the approaching footsteps. He yanked his boxers down, and kicked them across the room as he pulled the red panties out of the box. Dean didn’t even notice as the rest of his sacred panties spilled out across his floor. 

He yanked the red silk up and over his straining cock, letting out a pornographic moan as the silk incased his balls. “Fuck...” he sputtered out, having to squeeze his dick to keep from coming.   
“God that is one of the most gorgeous sights I’ve ever seen.” Castiel breathed out, licking his lips as he watched Dean adjust himself inside the panties. 

Dean spun around and grinned as he observed the blue eyed man leaning against the door frame, his cock clearly outlined inside his pants.

Slowly and provocatively, Dean slid up to the other man with a smirk that could make anyone come. He reached out and rubbed Castiel through his pants earning a surprised and beautiful moan from the blue eyed man. Castiel gripped the door frame with one hand to keep himself steady as his breathing got heavier. Dean’s hand felt amazing and Castiel knew he had to get out of his pants quick or they would be ruined. 

An animalistic growl escaped from between Castiel’s lips then as he shoved Dean back towards the bed. “Get on your hands and knees.” He commanded and Dean was almost too quick to respond. 

Scurrying to do as the other man commanded, Dean ended up slipping on the clothes on the floor and landing face first into the bed. 

A dark chuckle rang through the air as Castiel walked up behind the clumsy man and ran a hand up his spin. “So eager for me.” 

Dean gulped and hurried to pull his knees up underneath him. The bed sank under his weight and Dean rocked back and forth for a moment as he found his balance. 

Castiel stood back and watched, slowly dropping his own pants and underwear to the floor and giving himself a few strong stokes. The sight of Dean’s beautiful ass, wrapped in red lacy silk, framing each globe perfectly, was enough to drive any man crazy. 

Positioning himself behind Dean, Castiel ran his hand slowly from the base of the man’s spine to his balls. Dean shivered and let out a surprised moan as Castiel started to roll his balls around. Both men were sure they had never been this turned on before in their life. 

“Oh Dean, you are so beautiful...” whispered Castiel as he leaned over to lay kisses on the curve of Dean’s lower back. 

Dean felt a twist in his stomach at those words. No one had ever said something like that before, not with so much passion and blatant honesty behind it. There was nothing beautiful about him, not really. Maybe some good looks but that was about as far as it went. “Shut up... and just fuck me.” Dean stuttered out.

Castiel frown and removed his hand from where it was still fondling Dean. A whimper slipped out of the man at the loss of the contact but is quickly replaced by a surprised gasp when Castiel forcibly flipped him over onto his back. 

“Dean Winchester you listen to me right now,” Castiel growled out as he hovered over the other man’s body. “First off, I will take my sweet ass time with you, I am going to cherish every part of you until I have you a withering, beautiful mess under me because I have waited too long for this. Second off, you are gorgeous...” Castiel’s voice dropped down to a whisper as he cupped Dean’s face in his palm making sure the other man looked up at him, “You are the most gorgeous person I’ve ever met. Inside and out, and I haven’t even known you that long. But you are so passionate and caring, it is obvious to see when you talk about the things you love like your younger brother.” Dean made a face at the mention of Sam while about to have sex. Castiel shook his head with a smile and laid his forehead against Dean’s, “I will spend the rest of my time with you, however long that may end up being, convincing you that you are beautiful, if it’s the last thing I do.” 

Dean was pretty sure he had tears in his eyes at this point. No one had ever shown him so much love, so much care since his mother had died. It felt like there was a rock in his throat as he tried to speak but Castiel just leaned down to kiss him, taking any words of protest he had away. 

Their dicks had softened some during their brief moment, but were quick to rise again as Castiel rolled his hips against Dean’s. They both moaned into the others mouth, their breath mixing as pleasure swept through them. 

Castiel sat back up, his legs straddling Dean’s as he looked down to admire the man below him. A red blush spread across Dean’s neck and chest at the look Castiel was giving him but he grinned up at the other man and rolled his hips up to tease Castiel. 

Castiel raised an eyebrow in surprise and leaned down to slowly trail a line of kisses down Dean’s sternum to his belly button. 

Dean closed his eyes and laid his head back allowing himself to just enjoy the moment and forget about anything else, to lose himself in all things Cas. 

Castiel’s tongue followed Dean’s happy trail to the seam of the red panties. He slide his tongue along the inside of it, causing Dean to shiver. A wet spot formed in the center of the silk as pre-come oozed from the tip of Dean’s encased, throbbing dick. 

Castiel moved his mouth down to the wet silk and mouthed it, his blue eyes looking up at Dean for his reaction.

Dean’s hand’s quickly found their way into dark, messy brown hair as he let out a beautiful moan. “Fuck Cas, please.” He begged. 

Castiel only smirked and lowered the panties enough to allow the tip of Dean’s penis to slip out. Slowly, he ran his tongue along the tip, slipping it inside the slit and along the edge of the head. 

Dean couldn’t even form coherent words anymore as Castiel worshiped him with his tongue, slowly exposing more and more of Dean till the panties were around his thighs. 

Castiel sat up then and smiled, “It’s almost a shame to take these off you look so delicious in them, but they are in the way of what I really want.” And with that the red panties joined his companions on the floor of Dean’s room. 

Now both men were completely naked, sweat glistening on their chests and their breathe heavy in the heated room. Dean reached over and grabbed lube and a condom from his bed side table knowing it would be needed soon. 

Castiel smiled and crawled up to kiss Dean softly on the lips. For a moment they just laid there, their bodies pressed together, as they explored one another’s mouth. Castiel pulled back slowly, catching Dean’s lower lip between his teeth as he did so. 

He moved down to circle his tongue around Dean’s left nipple as he pushed the man’s knees up, exposing his eager hole. Castiel lifted his head long enough to apply a generous amount of lube to his fingers before starting back up on Dean’s nipples. 

Dean moaned and squirmed under Castiel, never having realized his nipples were so sensitive. His hole clenched for a moment when he first felt the coolness of the lube against it but quickly relaxed, allowing Castiel to push his first finger into Dean’ tight heat. 

“Fuck Dean...” Castiel groaned into the center of the man’s chest, his dick throbbing from just the thought of being inside of Dean. 

A laugh shook through Dean’s chest as he clenched teasingly around Castiel’s finger, earning another groan from the blue eyed man. Castiel glared up at Dean and shoved a second finger in causing Dean’s laugh to quickly die out as a loud moan ripped through the air. 

Now it was Castiel’s turn to smirk as he continued to kiss and worship Dean’s chest with his mouth, leaving a path of hickies along his rib cage. Cas worked his fingers in deeply, twisting and bending them until suddenly Dean was arching his back off the bed in surprise, a hoarse shout escaping from the back of his throat. 

“Mmmm found it,” Castiel said with a proud voice as he continued to stroke Dean’s prostate. Dean quickly turned into a withering, incoherent mess.   
“Cas... please... babe, I’m not going to last much longer,” Dean somehow managed to choke out. 

Castiel gave a few more pumps of his fingers before pulling them out. Honestly he wasn’t sure how much longer he could hold on either.   
“I know it’s easier to do this on your hands in knees, but I want to see your face.” said Castiel, as he slid the Condom onto his leaking, aching dick. 

Dean felt a shiver flow through his body just thinking about those blue eyes watching him as they fucked. “Just hurry.” 

Chuckling, Castiel once again positioned himself over Dean, placing the swollen head of his cock against Dean’s fluttering hole. Cupping Dean’s cheek with one hand, Castiel slowly pushed into the other man while starring into his endless green eyes. 

Dean closed his eyes and moaned at the feeling of being completely filled up. It was better than anything he had ever felt before. 

“Eyes open,” Castiel commanded, stopping his thrust and earning himself a whimper from the man underneath him. 

Dean’s eyes flew open and he gasped as Castiel quickly bottomed out. “Fuck... Cas... You’re huge.” Dean choked out getting use to the stretch but not finding it unpleasant. 

For a moment Castiel paused, afraid he had hurt Dean but the other man quickly urged him on with a roll of his hips, “Don’t you dare stop.” Dean spat out. 

“Wouldn’t dream of it,” Castiel said after making sure Dean wasn’t in any kind of pain. 

Pulling almost completely out, Castiel thrusted roughly back into Dean, causing the headboard of the bed to slam against the wall. Their pace picked up from there, it was fast, messy and dirty. The sound of slapping skin filling the thick, humid air accompanied by the pants and moans of the two men on the bed. 

It wasn’t long before Dean felt a tightness growing in his balls and he reached down to wrap a hand around his pulsing length. His hand never made it though. Castiel swatted it away and wrapped his own, long graceful fingers around Dean’s length. He quickly pushed the man over the edge and into an oblivion of pure bliss. Dean came with a hoarse shout, his hole clenching tightly around Castiel’s length. 

It was probably one of the most beautiful sight’s Castiel had ever seen, the sight of Dean’s back arching off the bed as he came, come covering them both. 

It didn’t take more than a few more thrusts for Castiel’s to feel his own release coming. Dean was still lost in his own little world and didn’t even feel the bite as Castiel dug his teeth into the meat of Dean’s shoulder as he came, his body heaving out more come then Castiel thought possible. 

With shaking arms, Castiel collapsed on top of the other man, wincing as his quickly softening cock slipped out of Dean. 

Once their breathing had come back to normal, Castiel pushed the damp hair from his face and looked up at Dean, “Sorry for the bite,” he said sheepishly, wiping away a small spot of blood. 

Dean shrugged, “I didn’t even feel it. Besides, I kind of like it. Makes me feel like you’re claiming me.” Dean admitted with a slight blush. 

Grinning widely, Castiel leaned up and kissed Dean slowly and passionately. It was unlike any of the other kisses they had shared that night. It felt as if Castiel was promising something to Dean, like this kiss meant there was more to come between the two sweaty men in bed together. 

Dean pulled back with a dopey grin, needing to breath. He reached over the edge of the bed and grabbed his boxers. After cleaning up what he could of the mess on his stomach, Dean threw the dirty boxers across the room towards the hamper while Castiel removed the condom with a grimaces and tossed it in the trash. 

Holding his arms open invitingly, Dean waited for Castiel to join him back on the bed. Happily, Castiel curled up against Dean’s chest, their legs tangling together. Dean tugged the comforter over them and nuzzled his face into Castiel’s still slightly damp hair. 

“Goodnight Cas,” Dean whispered out exhausted. Neither one of them questioned the fact that Castiel was obviously staying the night. They just settled in together like they had done it a thousand times before. 

“Goodnight beautiful.” Castiel whispered back before slipping off to sleep the happiest anyone could ever be.

**Notes for the Chapter:**

> Follow me on tumblr! Casorpiedeanwinchester


	9. Chapter 9

**Summary for the Chapter:**

> AND....  
> They all died,   
> Just kidding.

**Notes for the Chapter:**

> Hot Damn! I actually finished my first fic. Which is funny considering this whole fic started cause I wrote something quick for a friend with a panty kink. He, he. 
> 
> Well this is just a quick little conclusion chapter. 
> 
> THANK YOU ALL SO MUCH FOR READING THIS, I LOVE YOU -sends hugs and kisses- 
> 
> Please follow me on tumblr! casorpiedeanwinchester

**Six Months Later**

Dean pulled into the familiar spot in front of the coffee shop, a grin on his face. While he normally wasn’t the type of sappy guy who cared about anniversaries, today marked six months that Cas and him had been together. It had been by far the best six months of his life. There hadn’t been a single dull moment. The only part that scared Dean was that this was so far his longest real relationship; everyday he was just waiting for the other shoe to drop but so far nothing even close to that had happened.

Slipping out of the warmth of the Impala, Dean scurried into the cafe, flowers hidden under his jacket. At the sound of the bell, Castiel looked up from where he was leaning against the counter reading a paperback. A grin as wide as Texas spread across the blue eyed man’s face at the sight of his boyfriend.

Returning the smile, Dean whips the flowers out with a small bow and winks at his boyfriend. “For my prince, happy six months babe.”

Castiel’s blue eyes widened in surprise and he raised a hand to his mouth. No one had ever done anything so sweet for him before. Not even his past boyfriend who he dated for almost a year. Quickly, Castiel hopped up and slide across the counter, throwing himself at Dean.

Dean barely managed to keep the flowers from getting crushed as he caught Castiel in his arms and grinned into the enthusiastic kiss that was more teeth than anything.

Finally, Castiel pulled back allowing both of them to breath. He took the flowers from Dean and smelled them with a grin. “These are beautiful! Red and white chrysanthemums, love and truth. Plus tulips to declare your already known love for me, and a single red rose.” Castiel grinned and felt tears swell in his eyes. He knew Dean had taken the time to look up each one of these flowers meaning, and he knew they hadn’t been cheap to get.

Castiel grabbed Dean’s shirt and pulled him in for a passionate and gentler kiss. Dean sighed happily into it, his arm coming around the other man’s waist. They kiss until a cough breaks them apart and they look over to see Gabriel standing there making disgusting faces at them. “Alright you two, get out of here and quiet making my customers want to throw their breakfast up with your sappiness and lip locking.”

Castiel looked confused for a second since he was supposed to work all day today. Dean grinned and kissed his head, “I asked Gabriel to give you the day off,” he explained.

“You are seriously the best boyfriend ever!” Castiel exclaimed pecking Dean on the cheek before hurrying around the counter to put the flowers in some water and grab his coat.

Dean just smirked, “I know” he said proudly ignoring Gabriel’s scoff.

Helping Castiel into his jacket, the two boys wave goodbye to Gabriel and hurry through the cold into the car. Once settled in with the heat running, Castiel glanced over at his boyfriend, “So where to?” he asked knowing Dean already had the whole day planned out.

“Well,” Dean prompted giving Castiel a sly grin, “thought we could go shopping first. After all my collection can never be too large and I like having your input.”

Castiel blushed slightly but smirked, “Good, besides I don’t want anyone eyeing what’s mine.” He gave Dean a wink, earning a blush from the man as they pulled out of the parking spot.

Dean reached over and grabbed his boyfriends hand as they drove to the store, thinking about how in six months he went from hiding his panty kink from the world to going shopping for them with the most perfect boyfriend anyone could ask for; he wouldn’t have had it any other way.

**The End!**

 


End file.
